Certain addition reactions and products of certain divinyl ketones are known. Divinyl ketones have known polymerization capability.
British Pat. No. 1,421,597 (1976) (incorporated herein by reference) teaches the sizing of paper using mono-olefinically unsaturated comonomers containing one or more tertiary or quaternary nitrogen atoms such as mono-olefinically unsaturated carboxylates, 1-diethylamino-4-penten-3-one and 1-[N-(2-chloro-3-hydroxypropyl), 0-formyl-morpholinium]-4-penten-3-one. No methods were disclosed to prepare these comonomers.
Nazarov and various coworkers, CA 42:7727i; 7729i; 7738d; and 7739c (1948); and CA 43:6625a (1949) (each abstract incorporated herein by reference), teach the addition of aniline; malonic ester, acetoacetic ester and acetylacetone; hydrogen sulfide; alcohols; and hydrogen cyanide, respectively, to 5-methyl-1,4-hexadien-3-one. The addition was to the 1-ene bond in forming the straight-chain addition products. Hydrogen sulfide addition resulted in formation of 2,2-dimethyltetrahydro-1,4-thiapyrone.
Ivanova et al., CA 58:7819h (1962) (abstract incorporated herein by reference), teach the addition of an alkyl nitroamino group to the 1-ene bond of 5-methyl-1,4-hexadien-3-one and 1,4-hexadien-3-one.
Mirinov et al., J. Gen. Chem. USSR, 33(5), 1476-1480 (1963) (pages incorporated herein by reference), teach the preparation of certain 1-(diethylamino)-4-penten-3-one and 1-diethylamino-5-methyl-4-hexen-3-one by the hydrochloric acid catalyzed Mannich reaction of diethylamine hydrochloride, formalin and methyl ethyl ketone at 100.degree. C. The preparation of divinyl ketones based on the Mannich reaction is also taught.
Takemoto et al., CA 65:13834 h (1966) and Kogyo Kagahu Zasshi, 69, 524-526 (1966) (abstract; and pages incorporated herein by reference), discuss the reaction of divinyl ketone with thiophenol, thiolacetic acid, thiolbenzoic acid, aniline, piperidine, malononitrile and hydroxylamine. Both vinyl bonds in the divinyl ketone became saturated upon the addition of these compounds.
In addition, certain polymeric materials derived from divinyl ketones are known. It is known to employ the compound divinyl ketone (i.e., 1,4-pentadien-3-one) in certain polymerizations and as a cross-linker in certain polymeric materials.
For example, Chiang, U.S. Pat. No. 4,401,742 (1983) (incorporated herein by reference), teaches that divinyl ketone may be used as a monomer in the polymerization of a polymer used as a matrix to support pigmentive particles in a copying machine as a toner.
Castello et al., U.S. Pat. No. 460,477 (1984) and Amjad et al., U.S. Pat. No. 4,510,059 (1985) (both incorporated herein by reference), teach that unspecified divinyl ketones may be copolymerized with a cationic-containing monomer to make polyampholytes useful as cationic polymers or surfactants for silica scale inhibition in brines.
Howell et al., U.S. Pat. No. 4,246,386 (1981) and Colyer, U.S. Pat. No. 4,456,643 (1984) (both incorporated herein by reference), teach that divinyl ketone may be used in free radical copolymerizations with other vinyl resins to obtain a cross-linked vinyl copolymer useful as crush-resistant beads and as an ion-exchange resin support (Howell et al.) and sealant coating of a fibrous backing to a decorative laminate useful as a floor covering (Colyer).
What is lacking in these patents and publications and what is needed are certain monoadduct monomers from divinyl ketones and a process to prepare monoadduct monomers from divinyl ketones efficiently. What is additionally lacking in these patents and publications and what is needed are certain polyadduct polymers, especially as novel easily cured coatings and more especially from the monoadduct monomers or A- or B-stage resins derived from compounds such as divinyl ketones.